1: LiBr / dimethylformamide / 5 h / 80 - 100 °C 2: m-chloroperbenzoic acid / CH2Cl2 / 2 h / 35 °C 3: 1.) potassium tert-butoxide, 2.) HCl / 1.) THF, 15 deg C, 2 h; 2.) THF, 15 deg C, 20 min View Scheme

N-bromosuccinmide; meta-chloroperoxybenzoic acid in tetrachloromethane 6 h; Heating;

lithium bromide in N,N-dimethyl-formamide T=80 - 100°C; 5 h; Yield given;

1: LiBr / dimethylformamide / 5 h / 80 - 100 °C 2: m-chloroperbenzoic acid / CH2Cl2 / 2 h / 35 °C View Scheme

1: LiBr / dimethylformamide / 5 h / 80 - 100 °C 2: m-chloroperbenzoic acid / CH2Cl2 / 2 h / 35 °C 3: 1.) potassium tert-butoxide, 2.) HCl / 1.) THF, 15 deg C, 2 h; 2.) THF, 15 deg C, 20 min 4: 100 percent / H2 / Pd/C / tetrahydrofuran / 1.5 h / 2585.7 Torr / Ambient temperature View Scheme

hydrogenchloride; potassium tert-butylate 1.) THF; 2.) ice-cooling; Yield given. Multistep reaction;